Family Game Night
by IwillYURIforYAOI
Summary: Based on one of the million tumblr posts that describe AUs that need to happen. It starts with Sam, Dean, and John crowding around and playing Monopoly and will probably eventually expand to be the Winchester boys roping everyone into playing board games with them. Rated T for angry Monopoly language, but could probably pass for a K
1. Chapter 1

"Samuel Winchester, did you buy Boardwalk?" John exclaimed, digging through the pile of unclaimed property cards.

"Yeah, Dad," Sam said, holding up the dark blue card from his hand. "Pay up.

"I raised you dammit. I'm not paying this."

"Dad, it's the rules! You have to pay me."

"I'm not paying you, Sam. And that's that."

Sam threw his cards on the ground and stood up from his crouching position around the Monopoly board. "Dad, you owe me five hundred dollars and that's that!"

"Sam!" Dean snapped. All of his property cards and money were laid out in front of him, unlike John and Sam who insisted on holding their cards in their hands. It made the game a thousand times more difficult. "Sam, sit down. I swear to God if you walk out on the second Family Game Night in a row there will be hell to pay. And Dad! It's _fake_ money! And you have plenty! Just freaking pay Sam!" John sighed heavily and gave Sam a handful of bills.

Everything was silent as Dean rolled the dice. But as soon as he reached for his piece – the silver car, the one he had to permanently remove from the box and keep on him at all times to keep John from using it –

"Hey! Dad, you still owe me fifty dollars!"

Dean sighed and put his face in his hands. "This is worse than the time we played Headbandz."


	2. Chapter 2

**A/N: For you. You know who you are. Miss Needy. **

**For the rest of you (or, at least the readers in my head who I pretend read my stories) here you go! Part three is soon to come**

"I do not understand. We can move however many spaces we want to in real life."

"Well this isn't _like_ real life, Cas," Sam said, rolling his eyes toward Dean.

"You have to follow what the die says," Dean explained, rolling the die for his turn and moving the silver car on the corresponding number of spaces. "Then you either pay the person who owns the place or you can buy it yourself."

Cas looked down at his own piece – _Dean had thrown the top hat to him. He'd looked at Dean, confused. "This won't fit on my head."_ – then back up at Dean.

"But I do not have any need for the 'Ice Cream Shoppe.'"

"Cas, it's a _game_. The goal is to make the most money. So you kind of do need to buy _something_." Sam said. He'd never lost a game of Monopoly.

"But this isn't even real money."

"Cas, it's not based off real life," Dean explained for the millionth time. Cas sighed.

"Why are we doing this again?"

"Because Dean bet me that you could beat me," Sam informed him.

"Now come on, Cas," Dean said, leaning over the angel's shoulder, arranging Cas's cards in front of him. "We can take him!"

Four hours and a cheese pizza break later, Sam looked down at the cards in his hands. Which is to say, he looked down at his hands. They'd cleaned him out.

"Come on, Sam," Dean said smugly. "You owe Cas two hundred dollars. You landed on the Ice Cream Shoppe and he owns all the other purple properties."

"I don't _have_ two hundred dollars," Sam grumbled.

"Then you owe _me_ seventy-five dollars," Dean said, a huge cocky grin on his face. Sam had never lost a game of Monopoly, but Dean had never lost a bet. Cas still looked confused.

"I won?" Cas asked. Sam huffed out a breath. Dean continued to look incredibly amused.

"Yeah," Sam growled. "You won." He pulled out his wallet and gave Dean a handful of money he'd won from pool.

"Now who wants more pizza!" Dean exclaimed.


	3. Chapter 3

**A/N: Part three (and to date the last part). Enjoy, and if you have any ideas for what the boys should play next, please review!**

"Dean, what the hell is this?" John sighed, looking down at the box. Dean puffed up his chest.

"Headbandz. Everyone was playing it at school, so I took it. I thought it would be fun to play for family game night."

"Wow, Dean, that looks incredibly dumb," Sam commented, passing by on his way to the fridge. He rummaged around as John's face became red. If there was one thing John Winchester hated more than his son Sam was _agreeing_ with Sam.

"Well it's family game night. So sit down," John said, his nostrils flaring. Sam made epic bitchface #1 and sat at the table with an apple. As a group, they strapped the "headbandz" on their foreheads and stuck the cards into place. John was a pineapple. Sam was a reclining chair. And Dean was a head of lettuce.

"I don't get it!" Sam was shouting an hour later. "I'm brown, I move, and I'm large, but I'm not alive? What the hell am I?!"

"We can't _tell_ you Sam! You have to ask another question!" Dean exclaimed.

"Are you _shitting_ me?"

"No." John said shortly. He, too, was incredibly frustrated. "Dean, it's your turn."

"Um…" Dean said, a smirk on his face. He was enjoying this way too much. "Am I a bacon cheeseburger?"

"Dean. For the _thousandth time_. You are _not_ a bacon cheeseburger!" John yelled, his face beet red. "Ask a real question!"

"Am I brown?"

"No," Sam and John said exasperatedly in unison. They turned to each other and glared.

"Am I…" John considered. "A pineapple?"

Dean ripped the card off his forehead and looked at it. "You win," he said, like he really didn't care. "I am _so_ not a head of lettuce."

"How the hell was I supposed to guess _reclining chair_?" Sam exclaimed. "This game blows."

Dean and John agreed wholeheartedly.


End file.
